Deals on vacations and trips to Fleming Key

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Fleming Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was $1,113, price is now $580 per person
$580
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $28,685, price is now $13,722 per person
$13,722
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This aparthotel features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was $9,557, price is now $5,216 per person
$5,216
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.
The Local House

The Local House

3.5 out of 5
South Beach
Save 100% on your flight
Price was $1,784, price is now $1,000 per person
$1,000
per person
Dec 17 - Dec 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. A poolside bar, a coffee shop, and a terrace are also provided.
EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Save 100% on your flight
Price was $1,959, price is now $1,116 per person
$1,116
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury hotel features 2 restaurants, 4 outdoor pools, and a 24-hour gym. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. There's a hot tub on site, and a 24-hour front desk and a coffee shop are also provided.

Top Fleming Key hotels deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$265 nightly
The price is $298 total per night
$298 total
Oct 14 - Oct 15
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, poolside bar, and concierge services.
Pool
Hot Tub
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$166 nightly
The price is $187 total per night
$187 total
Oct 14 - Oct 15
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Hot Tub
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$205 nightly
The price is $231 total per night
$231 total
Oct 14 - Oct 15
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$202 nightly
The price is $227 total per night
$227 total
Oct 14 - Oct 15
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
$172 nightly
The price is $193 total per night
$193 total
Oct 14 - Oct 15
Total with taxes and fees
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.
On private beach
Pool
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$276 nightly
The price is $310 total per night
$310 total
Oct 25 - Oct 26
Total with taxes and fees
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.
On private beach
Pool
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Fleming Key?
Vacation packages, which include flights and hotels in Fleming Key, start from just $580. Make your travel dreams a reality and secure your vacation with Travelocity today.
Where can I get the best vacation package deals for Fleming Key?
One word — Travelocity. With no less than 400 partner airlines and 1,000,000 properties across the globe, it's a breeze to craft a Fleming Key package deal that fits your budget.
Why should I book my Fleming Key vacation bundle via Travelocity?
Nothing beats the feeling of knowing you've bagged the best price available — that's our Price Match Guarantee. Add to that our enormous range of destinations and 24/7 team of customer service professionals and you've got the formula for an unforgettable vacation.
Can I save on my Fleming Key car rental if I bundle it with my hotel or flight?
Certainly — and if you also add a tour to your Fleming Key vacation package, you'll pick up even greater savings. With an affordable package from Travelocity, you can find things to do around the region that interest you. Then, jump in your rental car and work your way through the list. Zoo Miami is one terrific sight to put on your itinerary. It's 110 mi from Fleming Key.
What is the best time of year to go to Fleming Key?
If you really want to wander wisely, is one of the best times to do it. That's when hotel rates are at their cheapest. In contrast, prices are at their highest around . January, February and March are the most popular times to vacation in Fleming Key, so expect long queues for famous attractions. Rather avoid the busy season? You'll find fewer crowds during August, September and October.

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